Process for chlorinating anthanthrone



Patented Apr. 25, 1933 UNITED STATES PATENT OFFICE RICHARD HERZ, OFFRANKFORT-ON-THE-MAIN, AND WERNER ZERWECK, OF FRANK-FORT-ON-THE-MAIN-FECHENHEIM, GERMANY, ASSIGNORS TO GENERAL ANILINEWORKS, IN 0., OF NEW YORK, N. Y., A CORPORATION OF DELAWARE PROCESS FORGHLORINATING- ANTHANTHRONE No Drawing. Original application filedNovember 1, 1926, Serial No. 145,697, and in Germany November 7, 1925.Divided and this application filed December 11, 1929. Serial No.413,419.

This application is a division of our copending application Serial N 0.145,697, filed November 1, 1926.

We have found that valuable vat dyestuffs of the anthanthrone series areobtainable by causing a chlorinating agent to act upon anthanthrone inthe presence of an inorganic diluent selected from the group consistingof: concentrated sulfuric acid, sulfuric acid monohydrate, fumingsulfuric acid, chlorosulfonic acid, sulfuryl chloride, sulfur chloridesand thionyl chloride.

As suitable chlorinating agents there may be used: chlorine gas andthose compounds which evolve chlorine during the reaction as, forinstance, sulfuryl chloride, antimony pentachloride, sulfur chlorides,alkali hypochlorites in the presence of an inorganlcacid and alkalichlorates in the presence of hydrochloric acid.

According to our new process, one or more chlorine atoms may beintroduced into the anthanthrone molecule by passing, while stirring,for instance, chlorine into finely ground anthanthrone in the presenceof an inorganic diluent as before stated, to whlch a small amount ofiodine, ferric chloride, antimony pentachloride, iodine-trichloride or asimilar compound may be added as a chlorine carrier.

The most valuable products are obtained when the chlorination is carriedout in such a way that approximately two atoms of chlorine enter intothe molecule of the anthanthrone.

The new dyestuif, thus obtained, having probably the formula:

from a violet vat violet shades, turning to a brilliant yellowish-orangeof excellent fasta ness When exposing the dyed goods to the air orsoaping it.

In order to further illustrate our inven tion, the following example isgiven, the parts being by weight and all temperatures in centigradedegrees, but it is understood that our inventionis not limited to theparticular products or reaction condition mentioned therein:

Ewa'mple Ola V 6 (approximately) is when dry an orange-red powder,soluble in concentrated sulfuric acid with a pure green color. It dyesvegetable fibers from a violet vat violet shades, turning to a brilliantyellowish-orange of excellent fastness when exposing the dyed goods tothe air or soapin which formula X is approximately the number 2, is whendry an orange-red powder, soluble in concentrated sulfuric acid with apure green color. It dyes vegetable fibers ing 1t.

We claim:

The process which comprises reacting at room temperature upon 15 partsof anthan-- throne with 16 to 20 parts of chlorine in the presence of200 parts of-chlorosulfonic acid and 0.2 parts of iodine.

In testimony whereof we ailix our signatures.

